A snow-covered town with a river running through it, surrounded by mountains and trees.

Find hotels in Winchester, NH from AED 251

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16 Aug - 17 Aug
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17 Aug - 18 Aug
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Our top choices for Winchester hotels

1. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Robert
AED 446
AED 498 total
includes taxes & fees
17 Aug - 18 Aug
Windmill Motel Restaurant

2. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
Canada
David
AED 327
AED 360 total
includes taxes & fees
23 Aug - 24 Aug
Econo Lodge Brattleboro South

3. The One Cat B&B

The One Cat B&B
Brattleboro
United States
marjie
AED 918
AED 1,010 total
includes taxes & fees
24 Aug - 25 Aug
The One Cat B&B

4. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Gary
AED 392
AED 432 total
includes taxes & fees
19 Aug - 20 Aug
Latchis Hotel

5. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
allisha
AED 596
AED 666 total
includes taxes & fees
17 Aug - 18 Aug
The Inn At Crumpin Fox

6. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
AED 1,083
AED 1,191 total
includes taxes & fees
20 Aug - 21 Aug
Inn on Putney Road

7. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
AED 1,106
AED 1,200 total
includes taxes & fees
17 Aug - 18 Aug
Chesterfield Inn

8. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Michael
AED 343
AED 373 total
includes taxes & fees
23 Aug - 24 Aug
Days Inn by Wyndham Keene NH

9. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Helen
AED 547
AED 594 total
includes taxes & fees
17 Aug - 18 Aug
Best Western Plus Keene Hotel

10. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Christopher
AED 554
AED 601 total
includes taxes & fees
3 Sep - 4 Sep
Hampton Inn & Suites Keene

11. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
James
AED 441
AED 478 total
includes taxes & fees
1 Sep - 2 Sep
Keene Elm City Hotel, an Ascend Collection Hotel

12. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Pauline
AED 557
AED 604 total
includes taxes & fees
15 Sep - 16 Sep
Riverside Hotel, an Ascend Collection Hotel

13. Colonial Motel

Colonial Motel
Brattleboro
United States
James
AED 274
AED 302 total
includes taxes & fees
17 Aug - 18 Aug
Colonial Motel

14. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Juli
AED 507
AED 591 total
includes taxes & fees
13 Sep - 14 Sep
Vikings Villages Resort

15. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Robert
AED 488
AED 537 total
includes taxes & fees
17 Aug - 18 Aug
Black Mountain Inn

16. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
VINCENT JOEL
AED 347
AED 382 total
includes taxes & fees
17 Aug - 18 Aug
The Covered Bridge Inn

17. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Marnie
AED 613
AED 675 total
includes taxes & fees
13 Sep - 14 Sep
Holiday Inn Express Hotel & Suites Brattleboro by IHG

18. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
AED 521
AED 565 total
includes taxes & fees
17 Aug - 18 Aug
The Carriage Barn Inn

19. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Morgan
AED 495
AED 544 total
includes taxes & fees
13 Sep - 14 Sep
Comfort Inn & Suites Brattleboro I-91

20. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
Brattleboro
United States
Emily
AED 228
AED 251 total
includes taxes & fees
17 Aug - 18 Aug
Travelodge by Wyndham Brattleboro VT
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Stay near popular Winchester attractions

Cass Pond

This serene 54-acre pond in Richmond offers peaceful fishing for bass, pickerel, and perch. Bring your own gear and a valid New Hampshire fishing license to fully enjoy this tranquil natural retreat.
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Winchester Speedpark

Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.
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Richmond Wildlife Manangement Area

This protected wilderness features diverse New Hampshire ecosystems across forests, wetlands, and meadows. Explore marked trails for wildlife viewing, especially during spring migration or autumn's foliage display.
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New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskeys while learning about the distillation process in a warm space adorned with reclaimed wood.
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Barden State Wildlife Management Area

This serene wildlife reserve in New Hampshire offers undisturbed natural landscapes for wildlife observation. Bring binoculars for spotting native species while exploring the peaceful trails during spring through fall.
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Conant Public Library

This historic 1892 library houses Winchester's heritage collection, including one of New England's earliest pipe organs. Browse artifacts or research local history with help from knowledgeable staff.
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Bennett Gorge

This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.
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Richmond Town Hall

This 1780 New England meeting house showcases traditional white clapboard architecture and historic timber framing. Explore one of New Hampshire's oldest civic buildings, listed on the National Register.
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Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
A snow-covered town with a river running through it, surrounded by mountains and trees.

Top Winchester Hotel Reviews

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"The staff was helpful. The room was clean. There plenty of options for breakfast. Would stay again"
charlene 1-night trip
Posted 7 hours ago
Hampton Inn & Suites Greenfield
Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Good location. Nice complimentary breakfast. Staff were friendly. Room was clean. As has been mentioned by other guests, there is a $300 security deposit which is refunded upon check out. Although staff stated it might take 2-3 business days for the refund to appear, mine was refunded the same day I checked out."
Sheree 1-night trip
Posted 9 hours ago
Hampton Inn Brattleboro
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Everything was great! Mary is an awesome bartender!!! We live in FL now and when we come back to visit we stay here!"
Kim 3-night trip
Posted 14 hours ago
The Colonial Hotel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"The front desk staff were friendly and engaged, the room was clean. That’s all we needed."
Morgan 1-night trip
Posted 1 day ago
Comfort Inn & Suites Brattleboro I-91
Windmill Motel Restaurant

Windmill Motel Restaurant

10/10 Excellent
"Just surprised how clean it was for the price"
Ross 1-night trip
Posted 2 days ago
Windmill Motel Restaurant
Vikings Villages Resort

Vikings Villages Resort

8/10 Good
"Christina was so kind and welcoming. The property is amazing, quaint, beautiful."
Gabrielle 2-night trip
Posted 2 days ago
Vikings Villages Resort
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"The room was clean and quiet and the air conditioning worked well. There is a full breakfast and a nice work out room. This is the second time I have stayed at this Best Western, and I will stay there again the next time I am in Keane NH."
Daniel 1-night trip
Posted 3 days ago
Best Western Plus Keene Hotel
The Putney Inn

The Putney Inn

8/10 Good
"I feel the 8.6 is much too overrated. A 7, maybe. Old building, needs a facelift. Clean, but does not feel as a happy place. Old rugs. Very dark ( but clean) rooms. Felt like in a cave. Manager had no people skills, not welcoming. Will not stay there again. Put a little money into the place!"
irina 1-night trip
Posted 7 days ago
The Putney Inn

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
AED 343
AED 373 total
23 Aug - 24 Aug
includes taxes & fees
7/10 Good! (1,002 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
AED 364
AED 406 total
17 Aug - 18 Aug
includes taxes & fees
Gardner Inn
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
AED 392
AED 432 total
19 Aug - 20 Aug
includes taxes & fees
Latchis Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
AED 441
AED 478 total
1 Sep - 2 Sep
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
AED 449
AED 494 total
9 Sep - 10 Sep
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
AED 495
AED 544 total
13 Sep - 14 Sep
includes taxes & fees
8.6/10 Excellent! (848 reviews)
Comfort Inn & Suites Brattleboro I-91

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Enjoy skiing, hiking, and exploring lush forests in Winchester's stunning nature reserves.
  • Charming Atmosphere: Stroll through picturesque streets that offer a warm and friendly vibe throughout the town.
  • Wine Tastings: Visit nearby wine country for delightful tastings and a refreshing getaway.
  • Family-Friendly Activities: Experience fun-filled attractions like the Dropzone Waterpark, perfect for all ages.
  • Cozy Accommodations: Choose from a range of hotels and charming bed and breakfasts for a comfortable stay.

Find great hotels near Winchester

Discover a range of hotel accommodations in Winchester, New Hampshire, perfect for every traveler. From cozy bed and breakfasts to modern hotels, you'll find options that cater to business needs, adventure seekers, and pet-friendly travelers. Explore the best hotels, room rates, and luxury accommodations to ensure a comfortable stay in this charming New England town.

  • Best Western Plus Keene Hotel: Located 17.7km from Winchester, the Best Western Plus Keene Hotel is a welcoming retreat for business travelers and families alike. This 3-star hotel prides itself on being LGBTQIA-friendly and offers a range of child-friendly amenities, including complimentary cribs. With a focus on comfort and convenience, guests can enjoy modern accommodations and easy access to local attractions, making it an ideal choice for both leisure and business trips.
  • Colonial Motel And Spa: Just 19.3km from Winchester, the Colonial Motel And Spa offers a unique spa-themed experience paired with pet-friendly accommodations. This 3-star motel features an onsite full-service spa, indoor pool, and hot tub, perfect for relaxation after a day of exploration. The property warmly welcomes pets and provides amenities such as a dog-only policy and waived fees for service animals. Guests can experience the best of both worlds with business-friendly facilities and a serene atmosphere.
  • Hampton Inn Brattleboro: Situated 19.3km away from Winchester, the Hampton Inn Brattleboro is an ideal choice for travelers looking for a blend of comfort and practicality. This hotel is LGBTQIA-friendly and accommodates pets, with policies that allow dogs and cats. Guests can expect top-notch service and amenities, ensuring a pleasant stay. The Hampton Inn offers easy access to the surrounding area, making it perfect for both business and leisure travelers seeking a welcoming atmosphere.

Where to stay near Winchester

Winchester, New Hampshire, offers a delightful blend of outdoor adventures and scenic relaxation. Stroll through its charming streets and experience the warm, friendly atmosphere that the city and its surrounding areas provide. Discover nearby wine country for a refreshing getaway, or enjoy leisurely walks in the picturesque landscapes. Whether you're seeking family-friendly activities or a romantic escape, Winchester promises an unforgettable experience filled with beauty and tranquility.

  • Brattleboro: Located 16.1km from Winchester, Brattleboro is a vibrant city that offers a unique blend of adventure and outdoor activities. Known for its scenic beauty, this area attracts visitors year-round, with peak seasons from July to September. Travellers flock here for skiing and various outdoor sports, taking advantage of the nearby ski fields and resorts. The local landscape features picturesque lakes and majestic mountains, along with the nearby national state park, making it a perfect destination for nature lovers and adventure seekers alike.
  • Keene: Situated 19.3km from Winchester, Keene is a charming city renowned for its stunning scenery and outdoor experiences. Similar to Brattleboro, it sees high visitor numbers during the warm months of July and August, as well as in October. Outdoor enthusiasts will enjoy the skiing opportunities at local resorts and the beautiful lakes and mountains in the vicinity. Additionally, Keene is home to a modern college university, adding a youthful energy to the area, making it a great spot for both relaxation and exploration.
  • Ashuelot: Just 3.2km from Winchester, Ashuelot is a quaint city ideal for those seeking a romantic getaway amidst nature. With a steady stream of visitors peaking during the summer and fall, this area offers a serene escape with its tranquil lakes, winding rivers, and rolling mountains. It's a perfect destination for couples and outdoor enthusiasts looking to enjoy peaceful hikes or scenic picnics, surrounded by the beauty of the New England landscape.

Things to do near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy activities such as skiing at local resorts, exploring scenic landscapes, and attending live music events. Don't miss the chance to experience wine tastings and the fun at Dropzone Waterpark, making it an ideal destination for an exciting and relaxing vacation.

Shopping

In Winchester, you can shop at Delectable Mountain Cloth for unique items. If you're up for a drive, check out the Vermont Marketplace for a vibrant shopping experience or the Brattleboro Farmers' Market for local goods and fresh produce.

Recreation

At Crumpin-Fox Golf Club, enjoy a round of golf surrounded by lush landscapes and luxury amenities, just 16.1km from Winchester. Experience vibrant live music at The Stone Church, located 17.7km away, offering an entertaining atmosphere. Brattleboro Country Club, 19.3km from Winchester, combines elegance with recreational golfing.

Adventure

The Metacomet-Monadnock Trail, located 9.7km from Winchester, offers stunning scenic views and adventurous hiking opportunities. For thrill-seekers, the Harris Hill Ski Jump, 17.7km away, provides an exciting skiing experience, while Granite Gorge, 19.7km away, is perfect for skiing enthusiasts looking for an exhilarating day on the slopes.

Nightlife

In Winchester, the nightlife scene is vibrant with options like Latchis Theatre, Hooker-Dunham Theater & Gallery, and New England Youth Theatre, all within 16.1km. Each venue offers a mix of romance, entertainment, and cultural experiences, perfect for an enjoyable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, visit during the cheaper months of March or December to January, and aim for a Tuesday stay, the least expensive day. Use Expedia’s search tool to filter hotels by price and type, including eco-certified options. Consider booking a package that combines your hotel, flights, and activities for additional savings. Lastly, explore free activities in the area and utilize public transportation where possible to keep costs down while experiencing the local culture.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are March and December to January, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to specify your budget, preferred location, and additional preferences. You can arrange your search results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to filter your choices by hotel type; for instance, selecting the “Eco-certified” filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Winchester hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, New Hampshire, offers a perfect getaway for those seeking outdoor adventures and scenic beauty. With its stunning nature reserves, lush forests, and serene parks, visitors can enjoy a romantic vacation filled with eco-friendly experiences. Whether you're hiking through the woods or relaxing in a park, Winchester provides a delightful escape into nature for travelers looking to connect with the great outdoors.

  • Moody Center: This institute, located 8.0km from Winchester, offers a serene environment ideal for reflection and personal growth. The center hosts various programs that encourage learning and community engagement, making it a perfect spot for those seeking a peaceful retreat.
  • Thomas Aquinas College: Situated 8.0km from Winchester, this modern college exudes vibrant city vibes. Visitors can explore its contemporary campus and appreciate its commitment to a classical education, enjoying a lively atmosphere filled with students and academic discussions.
  • Historical Old NMH Campus Building #3: Just 8.0km away, this historic building showcases rich culture and heritage. As you walk through its halls, you can sense the history and stories that have shaped the local community, making it a fascinating stop for history enthusiasts.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly SunnyAverageSlightly Low
February25.2°F (-3.8°C)Light RainMostly SunnySlightly LowAverage
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageSlightly High
June64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
July71.2°F (21.8°C)Light RainMostly SunnySlightly HighAverage
August69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
September61.9°F (16.6°C)Light RainMostly SunnySlightly HighSlightly High
October50.5°F (10.3°C)Light RainMostly SunnyAverageSlightly High
November38.7°F (3.7°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

For your trip to Winchester, New Hampshire, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is located 96.6km away, with nearby hotels like DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and the 4-star Simsbury 1820 House, 11.3km away. Manchester, NH (MHT-Manchester-Boston Regional) is 78.9km away, offering options such as The Grand at Bedford Village Inn, 6.4km from the airport, and DoubleTree by Hilton Manchester Downtown, also 6.4km away. Lastly, Worcester, MA (ORH-Worcester Regional) is 46.4km away, featuring hotels like Beechwood Hotel, 8.0km from the airport.

Frequently asked questions

What's the best place to stay in Winchester?
2 private mountain RV pads for rent. Full hook ups, located 2.1 mi (3.5 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Keene Elm City Hotel, an Ascend Collection Hotel and The Colonial Hotel. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Family Friendly Hilltop House In Putney Vermont: You might want to consider this vacation rental near Winchester, which is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.
What are some hotels with pools in Winchester?
Keene Elm City Hotel, an Ascend Collection Hotel: Provides buffet, an indoor pool, and complimentary wired internet access. The Colonial Hotel and Best Western Plus Keene Hotel are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is the best hotel near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
What is staying in Winchester like?
Visitors to Winchester are sure to enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Natural beauty is on display at Cass Pond, Royalston State Forest, and Rhododendron State Park. A couple of additional sights to add to your agenda are Winchester Speedpark and Pisgah State Park. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.